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Synthesis and rearrangement of 4-imino-4H-3,1-benzoxazines

Synthese und Umlagerung von 4-Imino-4H-3,1-benzoxazinen

Summary

N-Acylanthranilamides react with dibromotriphenylphosphorane in the presence of triethylamine as HBr captor to give 4-imino-4H-3,1-benzoxazines in good yields. If the reaction is carried out without acid acceptor, N-acetylanthranilamides yield 2-methyl-4-quinazolones, whereas N-benzoylanthranilamides give 2-phenyl-4-imino-4H-3,1-benzoxazines. It has also been found that 2-methyl-4-imino-4H-3,1-benzoxazines rearrange under the influence of HCl or HBr into the respective 2-methyl-4-quinazolones; 2-phenyl-4-imino-4H-3,1-benzoxazines, however, do not undergo such a rearrangement.

Zusammenfassung

Die Umsetzung von N-Acyl-anthranilsäure-amiden mit Triphenyldibromphosphoran in Gegenwart von Triethylamin als HBr-Akzeptor führt mit guten Ausbeuten zu 4-Imino-4H-3,1-benzoxazinen. Wird die Reaktion ohne säurebindendes Mittel durchgeführt, dann entstehen aus N-Acetyl-anthranilsäure-amiden 2-Methylchinazolone-4, jedoch erhält man aus N-Benzoylanthranilsäure-amiden 2-Phenyl-4-imino-4H-3,1-benzoxazine. 2-Methyl-4-imino-4H-3,1-benzoxazine erleiden unter dem Einfluß von HBr oder HCl eine Umlagerung in entsprechende 2-Methylchinazolone-4, während 2-Phenyl-4-imino-4H-3,1-benzoxazine zu einer solchen Umlagerung nicht befähigt sind.

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References

  1. Mazurkiewicz R. (1988) Monatsh. Chem.119: 1279;

    Google Scholar 

  2. Mazurkiewicz R. (1988) Pol. J. Chem.62: 115;

    Google Scholar 

  3. Mazurkiewicz R. (1988) Acta Chim. Hung.125: 831;

    Google Scholar 

  4. Mazurkiewicz R. (1988) Synthesis and Rearrangement of Imidic Anhydrides. In: Kováč J., Zálupský P. (eds.) Chemistry of Heterocyclic Compounds. Elsevier, Amsterdam, p. 415

    Google Scholar 

  5. Ugi I., Beck F., Fetzer U. (1962) Ber.95: 126

    Google Scholar 

  6. Kato T., Takada A., Ueda T. (1976) Chem. Pharm. Bull. (Japan)24: 431

    Google Scholar 

  7. Weddige H. (1887) J. Prakt. Chem.36: 150

    Google Scholar 

  8. Kolbe H. (1884) J. Prakt. Chem.30: 476

    Google Scholar 

  9. Korner W. (1887) J. Prakt. Chem.36: 159

    Google Scholar 

  10. Levy P. R., Stephen H. (1956) J. Chem. Soc.: 985

  11. Shah R. C. (1924) J. Indian Inst. Sci.7: 205; (1925) Chem. Abstr.19: 645

    Google Scholar 

  12. de Diesbach H., Jacobi O., Taddei C. (1940) Helv. Chim. Acta23: 469

    Google Scholar 

  13. Culbertson H., Decius J. C., Christensen B. E. (1952) J. Am. Chem. Soc.74: 4834

    Google Scholar 

Download references

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Mazurkiewicz, R. Synthesis and rearrangement of 4-imino-4H-3,1-benzoxazines. Monatsh Chem 120, 973–980 (1989). https://doi.org/10.1007/BF00808768

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  • DOI: https://doi.org/10.1007/BF00808768

Keywords

  • 4-Imino-4H-3,1-benzoxazines
  • Synthesis
  • Rearrangement
  • 4-Quinazolones